KR20180012958A - Method for preparing Epoxy Composition comprising Dicyclopentadiene - Google Patents
Method for preparing Epoxy Composition comprising Dicyclopentadiene Download PDFInfo
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
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- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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Abstract
Description
본 발명은 디시클로펜타디엔(Dicyclopentadiene: DCPD)형 화합물과 비스페놀형 에폭시 화합물을 용해시킨 주제 용액과 폴리아미드형 경화제를 용해시킨 용액을 반응사출성형법을 통해 DCPD를 함유하는 에폭시 수지 조성물을 제조하는 방법에 관한 것이다. The present invention relates to a method for producing an epoxy resin composition containing DCPD by a reaction injection molding method in which a solution obtained by dissolving a base solution in which a dicyclopentadiene (DCPD) type compound and a bisphenol type epoxy compound are dissolved and a polyamide type curing agent is dissolved .
구명정과 같은 소형 선박을 제조하는 데 있어서, 수분, 저온, 기계적 충격과 같은 외부의 환경으로부터 보호하기 위한 목적으로 에폭시 수지 조성물이 사용된다. 기존에는 DCPD, 텅스텐촉매(WCl6), 활성제(Et2AlCl)를 사용하여 개환 중합반응에 의해 poly-DCPD 수지를 제조하는 방법이 이용되어 왔다. 이러한 제조과정을 이용한 poly-DCPD 수지는 충격 및 굴곡 강도가 우수하고, 저온에서 내충격성이 우수하며 경화시간이 짧은(5분) 장점이 있으나, 중합 반응 시 대기 중에 노출되면 부분 중합(겔 또는 젤 상태)만 일어나고 완전 중합이 일어나지 않고, 또한 활성제(Et2AlCl)는 공기 중의 수분과 반응 시 폭발의 위험이 있는 문제점이 있었다. In manufacturing a small ship such as a lifeboat, an epoxy resin composition is used for the purpose of protecting it from external environment such as moisture, low temperature, and mechanical impact. Conventionally, a method of producing a poly-DCPD resin by ring-opening polymerization using DCPD, a tungsten catalyst (WCl 6 ), and an activator (Et 2 AlCl) has been used. The poly-DCPD resin using this manufacturing process has the advantages of excellent impact and flexural strength, excellent impact resistance at low temperature and short curing time (5 minutes). However, when exposed to air during the polymerization reaction, partial polymerization (gel or gel state) only taking place without complete polymerization occurs, and active agent (Et 2 AlCl), there is a problem that a risk of explosion during the reaction water and in the air.
본 발명자는 기존 방법의 문제점을 해결하면서 poly-DCPD 수지와 같은 기계적 강도를 갖는 수지 조성물을 개발하고자, DCPD 함유 에폭시 화합물(KDCP-130EK80, 국도화학), 페놀 수지 경화제 및 촉매(테트라 페닐 포르피린)를 혼합한 후 175℃에서 5 시간 동안 경화반응시켜 DCPD를 함유하는 에폭시 수지 조성물을 완성한 바 있다. 이러한 제조방법에 따르면 반도체 패킹용으로 사용 가능하고 수분 투과율이 낮은 DCPD 함유 에폭시 수지 조성물을 수득할 수 있었으나, 경화 조건이 가혹하다는 단점 때문에 실제 제조단계에서 사용하기에는 무리가 있었다. 이에, 기존의 poly-DCPD 수지와 동일한 기계적 강도를 가지면서 기존의 문제점을 해결할 수 있는 DCPD 함유 수지 조성물의 제조 방법을 연구한 결과, DCPD형 에폭시 화합물(KDCP-130, 국도화학) 및 비스페놀형 에폭시 화합물을 혼합한 주제 용액과 폴리아미드 수지 계열의 경화제 용액을 반응사출성형(Reaction injection molding, RIM)하여 DCPD를 함유하는 에폭시 수지 조성물을 제조하는 방법을 완성하였다. DISCLOSURE OF THE INVENTION In order to develop a resin composition having mechanical strength such as a poly-DCPD resin while solving the problems of conventional methods, the inventors of the present invention have found that a DCPD-containing epoxy compound (KDCP-130EK80, Kukdo Chemical), a phenolic resin curing agent and a catalyst Followed by curing reaction at 175 ° C for 5 hours to complete an epoxy resin composition containing DCPD. According to this manufacturing method, it is possible to obtain a DCPD-containing epoxy resin composition which can be used for semiconductor packing and has a low water permeability, but it has been difficult to use in an actual manufacturing step due to the drawback that the curing condition is severe. DCPD-type epoxy compounds (KDCP-130, Kukdo Chemical) and bisphenol-type epoxy resins were prepared by the same method as the conventional poly-DCPD resins, (RIM) of a solution of a curing agent based on a polyamide resin and a solution of a base material mixed with a compound of the formula (I) to prepare an epoxy resin composition containing DCPD.
본 발명의 목적은 (a) 디시클로펜타디엔(Dicyclopentadiene, DCPD)형 에폭시 화합물을 80 내지 100 ℃에서 용해시켜 A 용액을 제조하는 단계; (b) 경화제를 80 내지 100 ℃에서 용해시켜 B용액을 제조하는 단계; 및 (c) 상기 A 용액 및 B 용액을 반응사출성형하는 단계를 포함하는 DCPD 함유 에폭시 조성물을 제조하는 방법을 제공하는 데 있다. (A) dissolving a dicyclopentadiene (DCPD) type epoxy compound at 80 to 100 占 폚 to prepare a solution A; (b) dissolving the curing agent at 80 to 100 캜 to prepare a solution B; And (c) reactive injection molding the solution A and the solution B.
본 발명은 상기 목적을 달성하기 위하여, (a) 디시클로펜타디엔(Dicyclopentadiene, DCPD)형 에폭시 화합물을 80 내지 100 ℃에서 용해시켜 A 용액을 제조하는 단계; (b) 경화제를 80 내지 100 ℃에서 용해시켜 B용액을 제조하는 단계; 및 (c) 상기 A 용액 및 B 용액을 반응사출성형하는 단계를 포함하는 DCPD 함유 에폭시 조성물을 제조하는 방법을 제공한다. (A) dissolving a dicyclopentadiene (DCPD) type epoxy compound at a temperature of from 80 to 100 DEG C to prepare a solution A; (b) dissolving the curing agent at 80 to 100 캜 to prepare a solution B; And (c) reactive injection molding the solution A and the solution B.
본 발명에서, 상기 비스페놀형 에폭시 화합물은 25℃에서 점도 11,500 내지 13,500cps 인 비스페놀형 에폭시 화합물인 것을 특징으로 할 수 있다. In the present invention, the bisphenol-type epoxy compound may be a bisphenol-type epoxy compound having a viscosity of 11,500 to 13,500 cps at 25 占 폚.
본 발명에서, 상기 경화제는 25℃에서 점도 50,000 내지 70,000cps 인 폴리아미드형 경화제인 것을 특징으로 할 수 있다. In the present invention, the curing agent may be a polyamide type curing agent having a viscosity of 50,000 to 70,000 cps at 25 ° C.
본 발명에서, 상기 DCPD형 에폭시 화합물은 파우더 형태인 것을 특징으로 할 수 있다. In the present invention, the DCPD type epoxy compound may be in powder form.
본 발명에서, 상기 DCPD 함유 에폭시 조성물은 충격강도 값이 30 내지 45(kJ/m2)이고, 굴곡강도 값이 50 내지 70(MPa)인 것을 특징으로 할 수 있다. In the present invention, the DCPD-containing epoxy composition may have an impact strength value of 30 to 45 (kJ / m 2 ) and a flexural strength value of 50 to 70 (MPa).
본 발명의 일 실시예에서는 DCPD형 에폭시 수지로 적갈색 파우더 형태의 KDCP-130(국도화학)을 사용하고, 비스페놀형 에폭시 화합물로 점도 11,500 내지 13,500cps(25℃)의 YD-128를 사용하였으며, 경화제로 점도 50,000 내지 70,000cps(25℃)인 G-5022(국도화학)를 사용하였다. 다만, 본 발명의 내용은 이에 제한되지 않고 비스페놀형 에폭시 화합물로 저점도(100-500cps, 25℃) 타입의 비스페놀형 에폭시 수지(YD-113, YD-114F, YD-115J, 국도화학)로 변경 가능하고, 경화제는 폴리아미드 수지 계열의 저점도(500-1,000cps, 25℃) 수지(G-A0533, 국도화학)로 변경 가능하다. In one embodiment of the present invention, reddish brown powdery type KDCP-130 (Kukdo Chemical) was used as DCPD type epoxy resin, YD-128 having a viscosity of 11,500 to 13,500 cps (25 캜) was used as a bisphenol type epoxy compound, G-5022 (Kukdo Chemical) having a viscosity of 50,000 to 70,000 cps (25 占 폚) was used. However, the present invention is not limited thereto, and the bisphenol type epoxy compound may be changed to a low viscosity (100-500 cps, 25 ° C) type bisphenol type epoxy resin (YD-113, YD-114F, YD-115J, Kukdo Chemical) And the curing agent can be changed to a low viscosity (500-1,000 cps, 25 DEG C) resin (G-A0533, Kukdo Chemical) of a polyamide resin series.
본 발명에서, 비스페놀형 에폭시 화합물 YD-128은 주제 용액(A 용액)의 점성을 낮추고 경화 속도를 지연시켜준다. In the present invention, the bisphenol-type epoxy compound YD-128 lowers the viscosity of the subject solution (solution A) and delays the curing rate.
종래의 기술은 DCPD 함유 에폭시 수지 조성물을 제조하기 위하여 액상 타입의 KDCP-130EK80을 사용하고 있으나, 이 경우에는 테트라 페닐 포르피린 촉매를 사용하여 175℃에서 5 시간 동안 진행되어야 하고, 경화 반응 시 메틸에틸케톤이 증기로 발생하여 환경 처리 및 설비에 비용이 많이 소요되는 문제가 있다. 또한, KDCP-130EK80에 G-5022를 사용하여 50℃에서 1시간 동안 경화반응을 진행하면 스펀지처럼 변형되는 결과가 발생한다. In the prior art, a liquid phase type KDCP-130EK80 is used for preparing a DCPD-containing epoxy resin composition, but in this case, it is required to proceed at 175 ° C for 5 hours using a tetraphenylporphyrin catalyst, There is a problem in that it takes a lot of cost for environmental treatment and equipment due to this steam. Also, when the KDCP-130EK80 is cured at 50 ° C for 1 hour by using G-5022, the result is that it is deformed like a sponge.
본 발명에서는 종래 사용되는 액상 타입의 DCPD 함유 에폭시 화합물이 아닌, 파우더 형태의 에폭시 화합물을 사용함으로써, 환경 처리, 설비 비용, 가혹한 반응 조건과 같은 문제 없이 대기 중에서 우수한 효율로DCPD 함유 에폭시 수지 조성물을 제조할 수 있다. In the present invention, by using a powdery epoxy compound, which is not a conventionally used liquid type DCPD-containing epoxy compound, a DCPD-containing epoxy resin composition is produced with excellent efficiency in the air without problems such as environmental treatment, equipment cost, and severe reaction conditions can do.
본 발명에서 사용된 DCPD형 에폭시 수지, 폴리아미드 수지의 화학식은 다음과 같다:The formula of the DCPD type epoxy resin and polyamide resin used in the present invention is as follows:
[DCPD 형 에폭시 수지][DCPD type epoxy resin]
[폴리아미드 수지][Polyamide resin]
본 발명에 따른 DCPD 함유 에폭시 수지 조성물은 기존의 poly-DCPD 수지와 동일한 정도로 충격 및 굴곡 강도가 우수하고, 수분 투과율이 낮으며, 대기 중에서 제조 가능하다.The DCPD-containing epoxy resin composition according to the present invention has the same impact and bending strength as the conventional poly-DCPD resin, has a low water permeability, and can be produced in the air.
도 1은 ROMP에 의한 DCPD형 에폭시 중합 반응 과정을 나타낸 것이다.
도 2는 경화제 첨가량에 따른 충격강도 및 굴곡강도 값을 나타낸 것이다(phr(per hundred resin): 고분자(에폭시) 100중량(kg)당 첨가되는 경화제 중량(kg)).
도 3은 중합 온도에 따른 충격강도 및 굴곡강도 값을 나타낸 것이다.
도 4는 경화 시간에 따른 충격강도 및 굴곡강도 값을 나타낸 것이다. 1 shows a process of DCPD type epoxy polymerization reaction by ROMP.
Fig. 2 shows the impact strength and flexural strength values according to the addition amount of the curing agent (phr (per hundred resin): weight (kg) of the curing agent added per 100 kg of the polymer (epoxy)).
Fig. 3 shows impact strength and flexural strength values according to the polymerization temperature.
4 shows the impact strength and flexural strength values according to the curing time.
이하, 실시예를 통하여 본 발명을 더욱 상세히 설명하고자 한다. 이들 실시예는 오로지 본 발명을 보다 구체적으로 설명하기 위한 것으로서, 본 발명의 요지에 따라 본 발명의 범위가 이들 실시예에 의해 제한되지 않는다는 것은 당 업계에서 통상의 지식을 가진 자에게 있어서 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are only for describing the present invention in more detail and that the scope of the present invention is not limited by these embodiments in accordance with the gist of the present invention .
경화제 함량에 따른 Depending on the hardener content DCPDDCPD 함유 에폭시 수지 조성물의 제조 Preparation of Epoxy Resin Composition
적갈색 파우더 형태의 DCPD형 에폭시 수지 KDCP-130(국도화학) 200gr과 비스페놀형 에폭시 수지 YD-128(국도화학) 50gr을 85℃에서 용해시킨 후, 10분 동안 충분히 혼합시켜 주었다(A용액). 경화제 폴리아미드 수지 G-5022(국도화학)을 하기 표 1에서와 같이 첨가하여 85℃에서 완전히 용해시켰다(B 용액). 상기 제조된 A 및 B 용액을 반응사출성형법으로 몰드(50℃로 예열)에 주입하여 50℃에서 1시간 동안 경화시켰다. YD-128은 A용액의 점성을 낮추고 경화 속도를 지연시켜 주었다.200gr of DCPD-type epoxy resin KDCP-130 (Kukdo Chemical) in the form of reddish brown powder and 50gr of bisphenol-type epoxy resin YD-128 (Kukdo Chemical) were dissolved at 85 ° C and mixed thoroughly for 10 minutes (solution A). The curing agent polyamide resin G-5022 (Kukdo Chemical) was added as shown in Table 1 and completely dissolved at 85 캜 (solution B). The prepared solutions A and B were injected into a mold (preheated at 50 DEG C) by reactive injection molding and cured at 50 DEG C for 1 hour. YD-128 lowered the viscosity of the solution A and delayed the curing rate.
그 결과, G-5022 함량을 달리 첨가함에 따라 충격강도 및 굴곡강도 값이 차이를 나타내었다. G-5022 162gr 첨가한 경우에 충격강도는 34 kJ/m2, 굴곡강도는 62 MPa 를 나타내었고, G-5022 189gr 첨가한 경우 충격강도는 36 kJ/m2, 굴곡강도는 63 MPa 을 나타내었으며, G-5022 216gr 첨가한 경우 충격강도는 38 kJ/m2, 굴곡강도는 64 MPa 를 나타내었다. 이로부터, 기존의 p-DCPD 수지의 충격강도 값(46kJ/m2), 굴곡강도 값(76 MPa)와 비슷한 정도의 기계적 강도를 나타내는 것을 확인하였다. As a result, the impact strength and flexural strength value were different according to the addition of G-5022 content. The impact strength was 34 kJ / m 2 and the flexural strength 62 MPa when 182 g of G-5022 was added, and 36 kJ / m 2 and 63 MPa of flexural strength when 189 gr of G-5022 was added. , And 216 g of G-5022, the impact strength was 38 kJ / m 2 and the flexural strength was 64 MPa. From this, it was confirmed that the p-DCPD resin exhibited a mechanical strength similar to that of the conventional p-DCPD resin (46 kJ / m 2 ) and bending strength value (76 MPa).
중합 온도에 따른 Depending on polymerization temperature DCPDDCPD 함유 에폭시 수지 조성물의 제조 Preparation of Epoxy Resin Composition
DCPD형 에폭시 수지 KDCP-130(국도화학) 200gr, 비스페놀형 에폭시 수지 YD-128(국도화학) 50gr 및 경화제 폴리아미드 수지 G-5022(국도화학) 189gr을 사용하여 상기 실시예 1에서와 같이 A 및 B 용액을 제조하여 DCPD 함유 에폭시 수지 조성물을 제조하였다. 제조 온도를 70℃, 80℃, 90℃ 및 100℃로 달리하면서 충격강도 및 굴곡강도 값을 측정하였다., 200 g of DCPD type epoxy resin KDCP-130 (Kuko Kagaku), 50 g of bisphenol type epoxy resin YD-128 (Kuko Chemical) and 189 g of a curing agent polyamide resin G-5022 (National Kagaku Kagaku) B solution was prepared to prepare a DCPD-containing epoxy resin composition. The impact strength and flexural strength values were measured while changing the manufacturing temperature to 70 캜, 80 캜, 90 캜 and 100 캜.
그 결과, 온도 변화에 따라(70 내지 100℃) 충격강도 값이 34내지 37 kJ/m2, 굴곡강도 값이 61내지 64MPa로 나타났다. As a result, an impact strength value of 34 to 37 kJ / m < 2 > and a flexural strength value of 61 to 64 MPa were exhibited (70 to 100 deg.
경화 시간에 따른 Curing time DCPDDCPD 함유 에폭시 수지 조성물의 제조 Preparation of Epoxy Resin Composition
DCPD형 에폭시 수지 KDCP-130(국도화학) 200gr, 비스페놀형 에폭시 수지 YD-128(국도화학) 50gr 및 경화제 폴리아미드 수지 G-5022(국도화학) 189gr을 사용하고, 제조 온도 80℃에서, 경화 시간을 하기 표 3과 같이 변화시키면서 A 및 B 용액을 제조하여 DCPD 함유 에폭시 수지 조성물을 제조하였다. 50 g of bisphenol-type epoxy resin YD-128 (Kuko Chemical) and 189 g of a curing agent polyamide resin G-5022 (Kanto Chemical) were used, and the curing time Was changed as shown in Table 3 below to prepare A and B solutions to prepare a DCPD-containing epoxy resin composition.
그 결과, 경화 시간(1 내지 24시간)에 따라, 충격강도 값이 36내지 43 kJ/m2, 굴곡강도 값이 63내지 68MPa로 나타났다. As a result, the impact strength value was 36 to 43 kJ / m 2 and the flexural strength value was 63 to 68 MPa according to the curing time (1 to 24 hours).
Claims (6)
(b) 경화제를 80 내지 100 ℃에서 용해시켜 B용액을 제조하는 단계; 및
(c) 상기 A 용액 및 B 용액을 반응사출성형하는 단계를 포함하는 DCPD 함유 에폭시 조성물을 제조하는 방법.
(a) dissolving a dicyclopentadiene (DCPD) type epoxy compound at 80 to 100 占 폚 to prepare a solution A;
(b) dissolving the curing agent at 80 to 100 캜 to prepare a solution B; And
(c) subjecting the solution A and the solution B to reactive injection molding.
상기 비스페놀형 에폭시 화합물은 25℃에서 점도 11,500 내지 13,500cps 인 비스페놀형 에폭시 화합물인 것을 특징으로 하는 DCPD 함유 에폭시 조성물을 제조하는 방법.
The method according to claim 1,
Wherein the bisphenol-type epoxy compound is a bisphenol-type epoxy compound having a viscosity of 11,500 to 13,500 cps at 25 占 폚.
상기 경화제는 25℃에서 점도 50,000 내지 70,000cps 인 폴리아미드형 경화제인 것을 특징으로 하는 DCPD 함유 에폭시 조성물을 제조하는 방법.
The method according to claim 1,
Wherein the curing agent is a polyamide type curing agent having a viscosity of 50,000 to 70,000 cps at 25 占 폚.
상기 DCPD형 에폭시 화합물은 파우더 형태인 것을 특징으로 하는 DCPD 함유 에폭시 조성물을 제조하는 방법.
The method according to claim 1,
Wherein the DCPD type epoxy compound is in powder form.
상기 DCPD 함유 에폭시 조성물은 충격강도 값이 30 내지 45(kJ/m2)인 것을 특징으로 하는 DCPD 함유 에폭시 조성물을 제조하는 방법.
The method according to claim 1,
Wherein the DCPD-containing epoxy composition has an impact strength value of 30 to 45 (kJ / m 2 ).
상기 DCPD 함유 에폭시 조성물은 굴곡강도 값이 50 내지 70(MPa)인 것을 특징으로 하는 DCPD 함유 에폭시 조성물을 제조하는 방법.The method according to claim 1,
Wherein the DCPD-containing epoxy composition has a flexural strength value of 50 to 70 (MPa).
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| JP2001011289A (en) * | 1999-06-25 | 2001-01-16 | Matsushita Electric Works Ltd | Epoxy resin composition and semiconductor device |
| JP2002012653A (en) * | 2000-07-03 | 2002-01-15 | Denki Kagaku Kogyo Kk | Curable resin composition and metal-base circuit board using the same |
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| JP2001011289A (en) * | 1999-06-25 | 2001-01-16 | Matsushita Electric Works Ltd | Epoxy resin composition and semiconductor device |
| JP2002012653A (en) * | 2000-07-03 | 2002-01-15 | Denki Kagaku Kogyo Kk | Curable resin composition and metal-base circuit board using the same |
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